Acetyl chloride → 3'-Chloro-4'-fluoroacetophenone

HRID 1252582Notes

Reaction equation

HRID 1252582 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12].[C:13](Cl)(=[O:15])[CH3:14]>>[CH3:14][C:13]([C:10]1[CH:9]=[CH:8][C:7]([F:12])=[C:6]([Cl:5])[CH:11]=1)=[O:15]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 95831-Chloro-2-fluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5204223'-Chloro-4'-fluoroacetophenoneYield 76.7%

Conditions

Temperature
100 °C

Procedure

53.2 gm. (400 mmol) of aluminum chloride was carefully added in portions to a mixture of 26.2 gm (200 mmol) of 1-chloro-2-fluorobenzene and 31.2 gm of acetyl chloride at 50° C. After all the Lewis acid had been added, the reaction temperature was raised to 100° C. and maintained at that temperature for 3 hours. The hot reaction mixture was carefully poured onto ice and the resulting light-red oil twice extracted with ether. The combined ether extraacts were washed with saturated sodium chloride solution, dried and evaporated in vacuo to yield a crude brown oil. The oil was distilled to yield 26.47 gm of colorless oil.

Workup

  1. additionAfter all the Lewis acid had been added
  2. temperaturemaintained at that temperature for 3 hours
  3. additionThe hot reaction mixture was carefully poured onto ice
  4. extractionthe resulting light-red oil twice extracted with ether
  5. washThe combined ether extraacts were washed with saturated sodium chloride solution
  6. customdried
  7. customevaporated in vacuo
  8. customto yield a crude brown oil
  9. distillationThe oil was distilled

Sources & evidence

ORD record
ord-1ea734cb585d4a96924fd7d4564324bb
Source dataset
uspto-grants-1988_05
Patent number
US04743703

Reaction notes

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